I have a $106,000 mortgage to pay in 15 years at 5.375% interest. If I prepay $20,000 on the second mortgage payment, will I recoup the the same amount and more when I've paid in full?
Another way of asking your question is "will the total of my other payments be reduced by more than the $20,000 prepayment?
The answer is "Yes". Unless there is a prepayment penalty provision in the mortgage note that would penalize you for paying early, your early reduction of the loan balance would speed up the payoff of the loan and reduce your total of payments by more than the $20,000 you paid early.
Whether it would be to your advantage to make the prepayment would depend on the cost to you of the $20,000 payment. In other words, you would have to forgo the interest or investment income for the $20,000 in order to make that payment. That interest or investment income given up would be the cost of making the payment early.
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